39149-65-0

Upstream product

• 1694-31-1 tert-butyl acetoacetate 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 75-65-0 tert-butyl alcohol 
• 2382-59-4 2-methyl-3-oxobutanoic acid 
• 20487-40-5 tert-butyl propionate 
• 78191-00-1 N-Methoxy-N-methylacetamide 
• 88303-17-7 N-fluoro-N-2,2-dimethylpropyl-p-toluenesulfonamide 
• 74-88-4 methyl iodide 

Downstream Products

• 130203-08-6 (E)-3-{(S)-2-[(Diphenylphosphanyl)-methyl]-pyrrolidin-1-yl}-2-methyl-but-2-enoic acid tert-butyl ester 

Relevant academic research and scientific papers

Cu(I)/Chiral Bisoxazoline-Catalyzed Enantioselective Doyle-Kirmse Reaction of Allenyl Sulfides with α-Diazoesters

Herein, a Cu(I)-catalyzed enantioselective Doyle-Kirmse reaction of allenyl sulfides and α-diazoesters is reported, which provides an efficient synthetic route to enantio-enriched chiral tertiary homopropargylic sulfides. This reaction features high enantioselectivities (up to 96 % ee) and good functional group tolerance. The alkyl substituted α-diazoester has also been demonstrated as the efficient substrates in the asymmetric Doyle-Kirmse reaction. Mechanistic studies, including kinetic experiments, were conducted to gain insights into the details of the reaction pathway. The potential synthetic utility of this protocol has also been demonstrated.

Ru(ii)-Pheox-catalyzed Si-H insertion reaction: construction of enantioenriched carbon and silicon centers

We established a highly enantioselective Si-H insertion reaction to construct chiral centers at the carbon and silicon atoms, using a Ru(ii)-pheox catalyst. The catalytic asymmetric Si-H insertion reaction of α-methyl-α-diazoesters proceeded smoothly with excellent stereoinduction at both the neighboring carbon and silicon atoms (up to 99% yield and 99% ee).

Williamson Ether Synthesis with Phenols at a Tertiary Stereogenic Carbon: Formal Enantioselective Phenoxylation of β-Keto Esters

The enantioselective formation of α-aryloxy-β-keto esters is described for the first time. Lewis acid catalyzed enantioselective chlorination of β-keto esters and subsequent SN2 reactions with phenols yielded α-aryloxy-β-keto esters with up to 96 % ee. Favorskii rearrangement of α-chloro-β-keto esters was also found to give 1,2-diesters with slightly reduced enantiopurity.

Highly enantioselective catalytic 1,3-dipolar cycloadditions of α-alkyl diazoacetates: Efficient synthesis of functionalized 2-pyrazolines

Highly enantioselective 1,3-dipolar cycloaddition reactions of α-substituted diazoacetates are accomplished by catalysis of the chiral oxazaborolidinium ion. Functionalized 2-pyrazolines are synthesized in high to excellent enantiomeric ratios (up to >99:

Catalytic carbon insertion into the β-vinyl C-H bond of cyclic enones with alkyl diazoacetates

The first example of the boron Lewis acid catalyzed Csp2-H functionalization of cyclic enones was achieved using diazoacetates. The insertion of the carbon atom of diazoacetates utilizes BF3? Et2O or a newly designed oxaza

Catalytic enantioselective carbon insertion into the β-vinyl C-H bond of cyclic enones

Chiral oxazaborolidinium ion-catalyzed Csp2-H functionalization of enones using diazoacetate has been developed. Various β-substituted cyclic enones were synthesized in high yield (up to 99%) with high to excellent enantioselectivity (up to 99%

Enantioselective carbenoid insertion into phenolic O-H bonds with a chiral copper(I) imidazoindolephosphine complex

The enantioselective O-H carbenoid insertion reaction with a new chiral copper(I) imidazoindolephosphine complex has been developed. The chiral copper(I) complex catalyzed the insertion of carbenoids derived from α-diazopropionates into the O-H bonds of various phenol derivatives to give the corresponding α-aryloxypropionates with up to 91% ee.

Highly enantioselective chlorination of β-keto esters and subsequent SN2 displacement of tertiary chlorides: A flexible method for the construction of quaternary stereogenic centers

Highly enantioselective chlorination of β-oxo esters and subsequent stereospecific substitution of tertiary chlorides are described. Enantioselective chlorination of β-keto esters and malonates was performed using a chiral Lewis acid catalyst prepared from Cu(OTf)2 and the newly developed spirooxazoline ligand 2 to yield the desired α-chlorinated products with high enantioselectivity (up to 98% ee). Nucleophilic substitution of the resulting chlorides proceeded smoothly to afford a variety of chiral molecules such as α-amino, α-alkylthio, and α-fluoro esters, without loss of enantiopurity. The results of X-ray crystallographic analysis proved that Walden inversion occurs at the chlorinated tertiary carbon center. These results supported the fact that the substitution proceeds via an S N2 mechanism.

Substrate range of the titanium TADDOLate catalyzed asymmetric fluorination of activated carbonyl compounds

The substrate range of the [TiCl2(TADDOLate)] (TADDOL=α,α,α′,α′-tetraaryl-1,3-dioxolane-4, 5-dimethanol)-catalyzed asymmetric α-fluorination of activated β-carbonyl compounds has been investigated. Optimal conditions for catalysis are characterized by using 5 mol-% of TiCl2(naphthalen-1- yl)-TADDOLate) as catalyst in a saturated (0.14 mol/l) MeCN solution of F-TEDA (1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis- [tetrafluoroborate]) at room temperature. A series of α-methylated β-keto esters (3-oxobutanoates, 3-oxopentanoates) with bulky benzyl ester groups (60-90% ee) or phenyl ester (67-88% ee) have been fluorinated readily, whereas α-acyl lactones were also readily fluorinated, but gave lower inductions (13-46% ee). Double stereochemical differentiation in β-keto esters with chiral ester groups raised the stereoselectivity to a diastereomeric ratio (dr) of up to 96.5:3.5. For the first time, β-keto S-thioesters were asymmetrically fluorinated (62-91.5% ee) and chlorinated (83% ee). Lower inductions were observed in fluorinations of 1,3-diketones (up to 40% ee) and β-keto amides (up to 59% ee). General strategies for preparing activated β-carbonyl compounds as important model substrates for asymmetric catalytic α-functionalizations are presented (>60 examples). Copyright

COMPOUNDS AND COMPOSITIONS AS MODULATORS OF GPR119 ACTIVITY

The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of GPR119.